Organolithium reagents, reaction with aldehydes

The tosylhydrazone of an aldehyde RCHO gives the reductive alkylation product RCH2R on reaction with organolithium reagent R Li. Although yields are mediocre, the procedure is simple and is particularly well suited for the introduction of branched alkyl groups.Treatment of a tosylhydrazone with n-butyl-lithium followed by MesMX (M = Si, Ge, or Sn) gives the vinyl-silane,... 

Reaction with Organolithium Reagents (Section 16.5B) Reactions of aldehydes and ketones with organolithium reagents are similar to those with Grignard reagents. 

Metallated tosylhydrazones react with aldehydes and ketones to afford /8-hydroxytosylhydrazones in good to excellent yield. Further reaction with organolithium reagent gives the corresponding homoallylic alcohol (Scheme... 

Reaction of organolithium reagents with aldehydes and ketones (Section... 

Reaction of organolithium reagents with aldehydes and ketones (Section 14.7) Organolithium reagents react with aldehydes and ketones in a manner similar to that of Grignard reagents to form alcohols. 

Reactions of either Grignard or organolithium reagents with most aldehydes, ketones, or esters produce alcohols. Reactions of organolithium reagents with carboxylic acids, or of Grignard reagents with nitriles, produce ketones. 

Table 8.14. Cram Selectivity in Reactions of Organolithium Reagents with Ketones and Aldehydes...

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